13 Habits of Highly Effective Risk-Takers

By Nate Silver   GEAR Newsletter   DEC 19, 2024 4:00 AM

From poker players to venture capitalists, there’s a mindset to making the most of opportunities, and engineering the odds of success.

I played poker professionally before I ever wrote about politics or built an election model. What really fascinates me about gambling is the mindset that drives this behavior—a way of thinking that unites a cohort I call “the River.”

The River is a sprawling ecosystem of like-minded people that includes everyone from low-stakes poker pros to crypto kings and VC billionaires.

 It is a way of thinking—analytical, abstract, competitive, contrarian—and a mode of life. Most “Riverians” aren’t rich and powerful, but rich and powerful people are disproportionately likely to be Riverians.

I call the following the “13 Habits of Highly Effective Risk-Takers.” The quantitative risk-takers of the River and those who take physical risks—astronauts, deep-sea explorers, NFL players—have these traits in common. Based on my research, I hold the view that there is something hardwired in people who seek out risk and wrangle it successfully. How many do you share with them?

Successful Risk-Takers Are Cool Under Pressure

Being calm when other people lose their shit is a rare quality—and one that’s essential for a winning gambler. It doesn’t matter how well you execute in everyday situations—you’ll never reach the top of your craft if you choke when the pressure is on.

They Have Courage

In poker and sports betting, the vast majority of players lose money. To be at the very top requires a careful balance. Overconfidence can be deadly in gambling, but playing poker against the best is not for the faint of heart.

They Have Strategic Empathy

They put themselves in their opponent’s shoes—but don’t mistake this for the touchy-feely kind of empathy. In psychological studies, there’s a negative correlation between systematic thinking—what Riverians are skilled at—and empathetic behavior. Strategic empathy comes up a lot in poker—which is very much both a mathematical game and a people game.

They Are Process Oriented, Not Results Oriented

They play the long game. “Don’t be results oriented” is a mantra ingrained in many poker players. Yes, in the long run, results are what count, but one good thing about the River is that our compensation ultimately depends on objective measures.

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